The acid-catalyzed reactions of 4-chromanones with formaldehyde.

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概要

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• The reactions of several methyl substituted 4-chromanones, such as 4-chromanone (<B>1a</B>), 6-(<B>1b</B>), and 8-methyl-(<B>1c</B>), as well as 5,7-(<B>1d</B>) and 6,8-dimethyl-4-chromanone(<B>1e</B>) with formaldehyde were carried out in dioxane or mixed solutions of acetic acid and benzene or cyclohexane in the presence of sulfuric acid as a catalyst. The reactions involved an aldol condensation analogous to the Prins reaction, affording acetoxymethyl derivatives and 1,3-dioxanes. It was found that the formation of products was strongly influenced by the substituents on the 4-chromanones and solvents. In a mixed solution of acetic acid and benzene, <B>1b</B> and <B>1e</B> gave acetoxymethyl derivatives and 1,3-dioxanes, <B>1a</B> and <B>1c</B> only 1,3-dioxanes, and <B>1d</B> a resinous substance. In a dioxane solution, <B>1b</B> and <B>1e</B> gave 1,3-dioxanes, while <B>1c</B> gave a polymer. Bromination of <B>1e</B> in 35 and 96% sulfuric acids gave 3- and 5-bromo-6,8-dimethyl-4-chromanones, respectively. The acid-catalyzed reactions were compared with those in 96% sulfuric acid on the basis of the duterium exchange rates of 4-chromanones.

• 公益社団法人 日本化学会の論文

著者

• Nomura Ryoki

  Department Of Applied Chemistry Osaka Institute Of Technology

• Matsuda Haruo

  Department Of Applied Chemistry Faculty Of Engineering Osaka University

• Ninagawa Akira

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Nomura Ryoki

  Department of Petroleum Chemistry, Faculty of Engineering, Osaka University

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